Ultraviolet light filter composition



' Patented o; I

its year st r 1 orsie aizass paraavrorur mom, FILTER comosrrron Frits -E., Stockelbaclr, 'Montclair, N. J.

No Drawing. Application Apr-i117, 1937,

7 Serial No. 137,497 '1 :4 Claims. (cl. Isa-aci- My present invention relates'to 'a'class-of-new chemical compounds and totheir application as light'iilters for absorption of rays having wave lengths between approximately 2900 and 3200 5 Angstrom units. More speciflca y it-is directed to such compounds which are wa er soluble, nonirritating to the skin, relatively stable when exposed to'such rays and which can be readily and cheaply prepared; hence it isdirected to compositions especially adaptable for use in a lotion for preventing sunburn, reddening and blistering of the skin upon exposure to the sun.

In United States Patent No. 2,041,874, granted to me, there is disclosed the virtues and advantages of menthyl salicylate as a sunburn preventing means, Menthylsalicylate, however, is insoluble in water and hence must be incorporated in an oil or dissolved in alcohol for use in W able to use an ultraviolet filtering composition which iswater soluble, and. this is particularly so where the'sunburn preventing composition is to' be dispensed from a vending machine adapted v to deliver said composition in the form of a fine to spray which can lSedirectly applied to the parts 'of theLbody to be-ex'posed to the sunI Oily solu; 'tions are: at a disadvantageundersuch conditions,- and alcoholic solutions are excluded because, of their" infiammabllity. $0 A number of water havethe property of having wave lengths Angstrom units are, of

screening ultraviolet rays cfnirse, known and used to some extent butinearlyall' of said substances i cylate', which is water soluble. possesses this absorptlon property of ultraviolet light to a marked degree. .Thiswas established by preparing a" lotion. by dissolving 15' parts of trihydroxy- 'triethylamlne-salicylate in 85 parts of water and l determining the transmissio'n' factor thereof.

cosmetics and lotions. "In many cases it is desirsoluble substances which between 2900 and 3200 I I efi'ective, has a. decid-' iedl'y acid reactipn and is liable to cause 'irrita- R-salt quickly rleamine;- namely, trihydroxy-triethylamine-sali;-

-' cause of the To do this, a" film of about .08 to' .1 mm thickness, the normal thickness of a film which would be applied to the skin, was found to absorb about 92% of the light rays between the lines of the spectrum indicated by the wavelengths 2900 to- -3200 Angstrom units. While this is not quite et uallto the protection afiorded by menthyl sailcylate, practical tests made by application of this solution to the skin and exposure to ultraviolet light established the fact that the'protection 10 afiorded by this compound is quite adequate and furthermore, that it promotes the tan pigmentation' of the skin whereby additional protection to the ultravioiet raysis obtainable.

In view of he success obtained with trihy- 15 droxy-t'riethylamine-salicylate, I extended my researches to other compounds having the some organic base and found that the salts formed with ortho-cresotlnic acid and with ortho-betaable propertiesof the salicylate with respect to water'solubility and ultraviblet light absorption, v as described in the preceding paragraph.

In use as a preventive for'sunburn and as an aid in promoting tan pigmentation of the skin upon exposure to the sun, thevarious trihydroxytriethyl-amine salts which I have prepared and I each of which is athick, viscousliquid soluble dn bothwater and in alcohol, and miscible with ethylene glycol, diethyleneglycoland glycerine.

; may be appliedin either pure or diluted form" directly to the skin before exposure, or it may be applied after being made up Into a suitable lotion with any of the aforementioned solvents or miscible substances, or as a-cosmetic by admixture with suitable waxes-and oils to form a cream of proper consistency In whatever manner of appli cation the various aforementioned salts are applied to the skin, their eilectiveness is prima{ rily due tothe film of the particular salt'which 'formsmnthe skin upon'evaporatlon or absorption of the solvent 'or miscible liquid, which can functions. "as an, absorptive medium, screen or shield -.againstenetration therethrough of ultraviolet light ha 'inbefo're' stated, the various salts also function whenf thus applied in promoting tan pigmentar -tion'of'the skin under the influence of light be-.-

'Although' theproportion. of the hereinbefore described ligh't filter' compounds-i'n'the lotion, I

:crea'm orjother vehicle may vary'considerably, I y have found that a lotion containing approximate- 55 V hydroxymaphthoic acid also possessed the desir- 20 g I ng wave lengthsbetween approxi-" mately -;2 900 and 3200 Angstro units. Asherepresence of the amino group in saidso compounds-I. 1

'06 medi whichservesas a carrier for salt for Vessel until the acid completely dissolved and the resulting salt was formed. This salt, namely, trihydroxy-triethylamine-saligylate, is a reddishbrown viscous liquid which has a slight acid reaction and a pH value of approximatelyfi in a 5% water solution. 1 1 I The trihydroxy 9 triethyl ne-ortho-cresotingate and the 'trihydroxy-triethylamine-orthobeta-hydroxy-naphthoate, whic to my knowledge are also new chemical c mpoun'ds, were prred in -sulostantially thesam'e 'manner'as described hereinbeiore with respect to the salicylate by using :approtely the molecular weights of the various reacting substances after 'making due allowance for commercial grades or materials used. These compounds were likewise testedin the same manner ,as thesalioylate to tion of 10% dissolved in-water, both these salts caused almost. complete obscuration of thefwave droxy-naphthoatefiis a light yellow crystalline powder having a melting point oH25-l26 C.

' It will he noted that in the various'acidswhic I'have employed informing the ultraviolet light filter compositions, the hydrom'l and the carboxyl groups are in'ortho relation to one another.

From this I concluded that this particular configuration or relationship in ,the'acid might be fiecharacteristlc ofthe ultraviolet light absorptiomand in order to test out this theory'I prepared a salt by reacting controlling with respect to ethylemine. :the said compound being an isomer of the salicyl'ate hereinbeiore discussed. A, 10% solution 40f this para acid compound was prepared, and upon being tested was round'to transmit about of the wave lengths between 2900' in absorbing about 15% of light-betweensaid wave lengths. ms would appear to substantiate my hypothesis that vthe screening orrobscu'ring efi'ect obtained through such salts is. where the hydrow l rand "earlorthor relation to one another.

are in Having now fully and completely described my invention, and: the: manner in which it' is fto-be used? I do not, desire tobe limited to any specific manner or-inode .of application'oi the designated compounds to the slgin for the p described,

and hence in "the appended c where I have.

used the t "vehicle" it isto be understood that said term includes any solvent. oil, ore orother greases clroxy naphthoate.

'ortho relation. l. The compound -t facilitating its application to',- and disposition upon, the skin of a user. -It will 'aisohe apprecfi ated that the various salts enumerated. are not.

limited in their application to preventing sunburn or in aiding tan pigmentation of the skin, ut

, may also be used wherever an ultraviolet 1i htfilter is required forabsorbing the rayshaving wave lengths between approximately 2900 and 3200 Angstrom units;.for example, as a film upon any normal light transmitting medium.

What Iolaim is: 11-. An ultraviolet light filter for raysihaving wave lengths between approximately 2900 to 3200 dngstriimunits, comprising a film of a compound having the following formula 5 v canons. wherein R is gbnzene or naphthalene nucleus, and the hydroxyl group which is linked. to-the nucleus and'the carhoxyl group are in ortho relation. 91

2. An ultraviolet light filter for rays having I wave iength'hetween approximately 2900 to 3200'- detere their transmission factors of ultra- An violet light, and it was found that in a concentragstriiiniunitsl comprising a iilm of the com-- pound trihydroxy triethylamine -salicylate. 5

3. An ultraviolet 'ligfht-fllte'Lior rayshaving wave lengths between approximately 2900 to 3200 wave lengths between approximately 2900 to 3200 Angstrom units I comprising a'film oftheleompound trihydroxy-triethylamine-ortho-beta-hy- 4 5. A cosmetic for reventing sunburn, coni-= prising a compound ha png the following formula;

wherein R. is a henze'ne or naphthalene nucleus and the hydroxyl groupwhich is linked to-the nucleus and carhoml'groupare in-ortho relation; and 3200 Angstrom units and'was only efiective -.in ayeh'icle, and where'B is a. benzene or.naph-' thalene nucleus and the hydroxyl group which is linked to'the nucleus and carbonyl group are in I n; triethylamineortho-mtn hydrowenaphthoate. I

'- '5 s e to: i, 

